Organic nitrogen-fluorine compounds and their preparation

ABSTRACT

Dinitrogen tetrafluoride reacts with internally unsaturated acetylenes, e.g., hexafluoro-2-butyne, to produce isomeric fluoroimino fluoro amines and fluoro diamines, e.g.,   THAT CAN BE USED AS HIGH-ENERGY PROPELLANTS.

United States Patent [191 Sausen May 27, 1975 ORGANIC NITROGEN-FLUORINE COMPOUNDS AND THEIR PREPARATION [75] Inventor: George N. Sausen, Wilmington, Del.

[73] Assignee: E. I. du Pont de Nemours and Company, Wilmington, Del.

[22] Filed: Sept. 12, 1961 [2]] Appl. No.: 137,507

[5 6] References Cited UNITED STATES PATENTS 3,239,518

3/1966 Winberg 260/465.5 R X 3,347,898 10/1967 Peterson 260/4655 R 3,439,017 4/1969 Stevens 260/5705 PA X 3,700,708 10/1972 Petry 260/465.5 R X Primary ExaminerJoseph P. Brust [57] ABSTRACT Dinitrogen tetrafluoride reacts with internally unsaturated acetylenes, e.g., hexafluoro-Z-butyne, to produce isomeric fluoroimino fluoro amines and fluoro diamines, e.g.,

C C CF CF3 C CF CF3 and C1 3,

that can be used as high-energy propellants.

20 Claims, No Drawings ORGANIC NITROGEN-FLUORINE COMPOUNDS AND THEIR PREPARATION This invention relates to, and has as its principal objects provision of, novel compositions of matter con- 5 taining nitrogen and fluorine and a method for the preparation of the same.

Compounds containing nitrogen-fluorine (NF) bonds are of interest as high-energy propellants, polymerization initiators and intermediates in chemical syntheses. Relatively few N-F compounds of any kind have been reported and it is therefore desirable to extend knowledge of this field. Known organic N-F compounds are for the most part highly fluorinated, and very few such compounds with more than one NF moiety are known.

It has now been found that compounds containing NF moieties on adjoining carbon atoms can be prepared by reacting dinitrogen tetrafluoride (N F with disubstituted acetylenes. The reaction can be represented by equation (1):

NF w I -C-X, tqhez-e X is halogen; cyano, 6N; hydrocarbyloxycarbonyl,

-C-0Qi carbamoyl, 42-1114 hydrocarbyloarbamoyl, -C-NHQ; and

dihydrocapbyloarbamoyl, -c-N Where Q and Q are the same or different monovalent hydrocarbyl groups (e.g., methyl, tertbutyl, cyclohep- W -naphthyl, dodecyl), and where, in the formula 2 Q and Q can be joined together to form a divalent hydrocarbyl group (e.g., ethylene, 2,5-dimethylhexamethylene, 3-phenylpentamethylene).

Still further: halocarbonylhydrocarbyl,

cyanohydrocarbyl, -R"-CN; hydrocarbyloxycarbonylhydrocarbyl,

carbamoylhydrocarbyl,

hydrocarbyl-carbamoylhydrocarbyl,

ll R C NHQ,

and dihydrocarbylcarbamoylhydrocarbyl,

where X, Q, and Q are as above and R is divalent hy' drocarbyl such as methylene, undecamethylene, 2- butynylethylene, 1,3-phenylene, and the like.

Additional specific groups illustrative of the last two paragraphs are methoxycarbonyl, isopropylcarbamoyl, 4-methylphenoxycarbonyl, azacyclododecanel carbonyl, ethoxycarbonylmethyl, 4- chlorocarbonylbutyl, 2-phe'noxycarbonylethyl, llcarbamoylundecyl and the like.

Because of easy availability and high reactivity, a preferred class of products comprises those defined above in which R and R each contain l-l 2 carbons. An especially preferred class is that in which R and R are the same or different and are hydrocarbyl, halohydrocarbyl, carbamoyl, hydrocarbylcarbamoyl, or dihydrocarbylcarbamoyl groups of 1-12 carbons; cyano; or halocarbonyl.

The process of this invention leads to a mixture of the isomeric products I, II, and III, When R and R are the same, products I and II are identical. In addition, product III can exist in the form of cis and trans isomers. The relative amounts of products I, II, and III (or I and III) vary, depending on the acetylenic reactant and the reaction conditions, especially temperature.

Generically, products I and II can be named as fluoroimino fluoro amines; product III, as a fluoro diamine. As a specific example, the products I, II, and III from methylphenylacetylene (R =CI-I R C I-l can be named N,N, l -trifluoro-2-fluoroimino- 1 phenylpropylamine, N,N,1-trifluoro-2-fluoroimino-2- phenylisopropylamine, and N,N,N',N'-tetrafluoro-l- ..Uphenyl-l,2-propenediamine, respectively. For convenience, the products are represented hereinafter by structural formulas.

The mole ratio of reactants in the process of this invention is not critical. Usually an approximately 1:1 mole ratio is used, in accord with the stoichiometry of equation (1). An excess of either reactant can be used if desired, for example, to effect essentially complete conversion of the other reactant. Excess N 1 is easily removed from the product mixture by virtue of its volatility (b.p. 73C.).

A solvent is not required, but a solvent inert to the reactants and products may be used if desired. Use of a solvent is advantageous when the acetylenic reactant is a solid. Suitable solvents include hydrocarbons and fluorinated or chlorinated hydrocarbons, such as benzene, heptane, cyclohexane, petroleum ether, chlorobenzene, carbon tetrachloride, hexafluoropropene dimer, 1,2-dichloroethane, 1,1,1-trichloroethane, and 1,1 ,2-trich1oro-1,2,2-trifluoroethane.

The reaction temperature is likewise not critical. The preferred range is 25225C.' The reaction proceeds at temperatures below 25C., but usually at too slow a rate to be of practical value. Temperatures from 225C. up to the decomposition point of the product can be used if desired, but no advantage results.

The process is conveniently carried out at the autogenous pressure of the reactants in a closed vessel equipped with means of agitation and of measuring internal pressure. The inner surface of the vessel is resistant to chemical attack by nitrogen fluorides and hydrogen fluoride. Surfaces of stainless steel and Hastelloy C are suitable. Hastelloy C is the trade name of a well-known alloy of nickel, iron, and molybdenum.

The time required for the process varies with the acetylenic reactant and the temperature. The course of the reaction can be followed by observing the pressure drop as the reactants combine. When the pressure no longer falls, the reaction is complete. Under the preferred conditions, reaction is usually complete in onehalf to 6 hours. The products are separated by known procedures such as distillation or preparative-scale gas chromatography and filtration and recrystallization in the case of solids.

The products of this invention are distillable liquids or crystallizable solids. They are stable to air and moisture except when the groups R or R or both contain functions, e.g., fluorocarbonyl,

v trated by the following examples, in which all parts are by weight and pressures autogenous unless otherwise indicated.

EXAMPLE 1 NF NF:

NFa F To a Hastelloy C-lined shaker tube with a volume equal to that of parts of water were charged 10 parts of hexafluoro-Z-butyne and 11.7 parts of N F The tube was heated at for 1 hour with shaking. The mixture was distilled into a cylinder cooled at -1 96C., and unreacted starting materials were volatilized from the mixture at 78, after which the liquid residue amounted to 15.9 parts. Gas-chromatographic analysis of this liquid showed it to be principally (92%) a 58/42 mixture of trans/cis isomers of A minor amount (1%) of the isomeric NF NF was also present.

The trans and cis isomers were separated and purified by preparative-scale gas chromatography. The trans isomer was obtained as a colorless liquid, b.p. 49C. Mass spectrometic analysis showed m/e 247* as the largest fragment (parent-lF), and infrared analysis showed major absorption bands at 8.25;; (C-F) and 1 1.2 and 11.4p. (NF). Fluorine n-m-r (nuclear magnetic resonance) showed two resonance peaks in a area ratio at 6347 cps. and 527 cps. (56.4 mc., 1,2- dichlorotetrafluoroethane=0). The cis isomer was also obtained as a colorless liquid, b.p. 56C. Molecularweight determination by the gas-density method gave a value of 271; calcd. 266. The infrared spectrum showed absorption bands for C-F (8.011.) and N-F (11.35, 11.75p.) and also a 6.15p. band for carboncarbon unsaturation. Fluorine n-m-r showed two peaks in a area ratio at 6510 cps. and 396 cps. (56.4 mc., 1,2-dichlorotetrafluoroethane=0) in agreement with the above structure.

The isomeric product was obtained as a colorless liquid, b.p. 47C.

Anal. Calcd. for C F N F, 71.4; M.W., 266.

Found: F, 71.30; M.W., 268. 71.56

Infrared absorption showed C-F (8-8.25/1) N-F (10.511.5#), and C=NF (6.15p.). Fluorine n-m-r showed five resonance peaks at 5045, 3610, 55, +356, and +4153 cps. (40 mc., 1,2-dichlorotetrafluoroethane=0), in agreement with the above structure.

The hexafluoro-Z-butyne of this and the next succeeding example was obtained by the reaction of 2,3 dichlorohexafluoro-2-butene with zinc by the method of U.S. Pat. No. 2,546,997.

The shaker tube of Example 1 was charged with 9 parts of hexafluoro-2-butyne and 5.6 parts of N F and the tube was heated at 190-198 for 4 hours with shaking. The products were isolated as in Example 1. The principal product obtained from this reaction was a colorless liquid boiling at 47C. Gas-chromatographic analysis showed it to be a mixture of The shaker tube of Example 1 was charged with 3.6

parts of dicyanoacetylene and 104 parts of N F and the tube was heated at 140 for 3.5 hours with shaking. The gaseous product consisted largely of unchanged N F the liquid product amounted to 5.1 parts. Gaschromatographic analysis of this liquid showed it to contain NF NFa NC-C CF-CN as a principal component. This product was separated and purified by preparative-scale gas chromatography to give NF NF NC-C CF-CN as a colorless liquid, b.p. 82C.

Anal. Calcd. for C F N N, 3l.l; F, 42.2.

Found: N, 30.80; F, 41.89.

Fluorine n-m-r showed peaks at 8680 cps., a doublet at 5634, 5620 cps., and a triplet peak centered at +3949 cps. (56.4 mc., 1,2-dichlorotetrafluoroethane=O) in agreement with the above structure. Infrared analysis showed saturated CN (4.42p.) and C=NF (6.22,.L). Analytical gas chromatography indicated that the product contained 5-l0% of the isomeric EXAMPLE 4 A shaker tube like that of Example 1 was charged with 8.5 parts of diphenylacetylene, 29 parts of hexafluoropropene dimer, and 5.2 parts of N F The tube was sealed, heated at for 3 hours with shaking, allowed to come to room temperature, and opened. The brown liquid product was decolorized by filtering it through acid-washed alumina with the help of petroleum ether. The solvent was evaporated and the residue was distilled to give 4.6 parts (34%) of a mixture of with a minor proportion of as a yellow liquid, b.p. 98 (0.3 mm.); n 1.5272.

Anal. Calcd. for C H N F Fluorine n-m-r showed a single peak at 5934 cps. (C=NF), a weak-strong-weak pattern at 5800, 5228, 5076, 4501 cps. (CNF and a peak at +5098 cps.

(56.4 mc.; l,2-dichlorotetrafluoroethane$).

EXAMPLE 5 The shaker tube of Example 1 was charged with 1 1.7 parts of phenylpropiolyl fluoride and 9.2 parts of N F The tube was sealed, heated at 70 for 2 hours, allowed to come to room temperature, and opened. On distillation of the brown, liquid product there was obtained 13 parts (55%) of a mixture of together with a minor proportion of Cans-C C-COF,

as a colorless liquid, b.p. 6768 (6.0 mm.), which was sensitive to moist air because of the COP group but was stable under an atmosphere of nitrogen. The infrared absorption spectrum showed maxima at 5.36 1.

and 6.12;.L (C=NF).

Fluorine n-m-r showed a peak at 6896 cps. (C=NF), a peak at 6475 cps.

each of them split into doublets by each other, a weakstrong-strong-weak pattern at 5760, 5164, 5104, -4580 cps. (CNF and a peak at +4985 cps.

(56.4 mc.; l,2-dichlorotetrafluoroethane=0).

An anilide, in which the COF groups were replaced by --CONHC H groups, was prepared by adding aniline to an ether solution of the mixture; m.p. l66.5-l67.5, after recrystallization from cyclohexane.

Anal. Calcd for C H N EO:

C 55.38 H, 3.41; N, 12.92; Found: C, 55.64, H, 3.72; N, 12.56;

Similarly, the COF groups can be converted to other types of carbamoyl groups by reaction with ammonia or other amines. For example, ammonia converts the COF groups to CONH groups; dimethylamine, to CON(CH groups; and hexamethylenimine, to

groups.

EXAMPLE 6 can -c CF-Clig and C H -CF C-CH together with a minor proportion of as a colorless liquid, b.p. 74-76 (3.0 mm.)

Anal. Calcd. for C H N R:

Fluorine n-m-r showed a single peak at 5875 cps. chloride, and 3.5 parts of N F The tube was sealed, (C=NF), a weak-strong-strong-weak' pattern at 5925, heated at 75 for 3 hours, and] allowed to come to room 5355, 5251, 4679 cps. (CNF and a peak at temperature overnight. The solvent was evaporated +5199 cps. split into a triplet and the residue distilled to give a mixture of 1 1 1 11 c H CEC-G--GF-C 11 H C5C-CF-C-C H d which correspond to theisomer 6 5 6 5 6 5 6 5 an NF2 NR2 I 1 Ti C61-X5-CEC-C 12-0 11 calls-CF C-CH3.

l5 Peaks at 6135 cps., 5291 cps., and +4128 cps. are as a y l q -p- 140C The infrared attributed to the other isomers (56.4 mc.; 1,2- orp i Spectrum had a maximum at M dichlorotetrafluoroethane=O). EXAMPLE 9 EXAMPLE 7 i CHa-CEC-CEC-Cl-l 11 1 GF3-CEC-CF2CF2CF2CF3 11 13,,

"F2 NF NF NFZ fi TF2 TF2 l luae TF2 CH -CECCFC-CH 011 F- 11 3 I 3 H s C C cr -c-ei -c r cr' -cr -c-c r CF3-C c-c r 11F NFE cas-czc-c C-CHa The shaker tube of Example 6 was charged with 12.5 The Shaker tube of Example 1 was charged with parts of dimethyldiacetylene, 23 parts of carbon tetra- Parts of p p y 15 Parts Of a blend of hl ide d 19 pal-ts f N 1? T b was sealed 0 completely halogenated chlorofluorocarbons, and 8.7 heated at 70C. for 3 hours, and allowed to come to Parts Of 2 4 and the ube as heated at 186 for 3 room temperature. The solvent was evaporated, and hours with Shaking The Volatile liquid Product was pthe dark-brown residue was distilled to give 12.3 parts armed y distillation from the highef'boiling Chloro- (42 5%) of a mixture f fluorocarbon oil; it amounted to 8.7 parts of NF: NF NF NF: 111 TF CH -CnC-CF--C-CH and CH -C8C-GCFCHs CF 4 C-CF2CF2CF2CF3 together with a minor proportion of together with mmor amounts of 011 -050-0 C-Cl'la, 45

as a colorless liquid, b.p. 7273 (27 mm.); n

1.4041. The infrared absorption spectrum had a maximum at 44,, (C a C The ma or product was separated and purlfied by preparative-scale gas chromatography to give Anal. Calcd. for C6HGN2F4: T I 1% c, 39 56; 11, 3.32; N, 15.38; F, 41.73 Found: c, 40 11; H, 3.21; N, 15.71; F, 41.32

as a colorless liquid, b.p. 114C. EXAMPLE 8 C5H5CEC-CEC'CH5 N F 60 Anal. Calcd. for c,F,,N,= F, 73.0 2 1 Found: F, 73.34 e 5-CECCCF-C H 4' C 1'l C:C-CFJ-C H NP: NF: Fluorine n-m-r showed seven peaks at 6445 cps.

(C--NF 6374 cps. (CNF 573 cps. (CF +913 cps. (CE), and peaks at +2106, +3015, and

The shaker tube of Example 1 was charged with 5.0 +3418 cps. for CF groups (56.4 mc., 1,2-difluorotetraparts of diphenyldiacetylene, 15 parts of carbon tetrachloroethane=0) in agreement with the above struc- 1 l ture. Infrared analysis showed principal absorption bands at 88.5[L (C-F) and 11.2511. (NF) with weak absorption in the C=C region (6n), also in agreement with the above structure.

The perfluoro-2-heptyne used in this example was prepared as follows:

A mixture of 69 parts of trifluoromethylacetylene (made from propiolic acid and SF, by the method of Hasek, Smith, and Engelhardt, J. Am. Chem. Soc. 82, 543 (1960)) and 275 parts of perfluoro-n-butyl iodide (commercially available) was heated for 10 hours at 10 the mixture during the addition and subsequent heating. It was purified by precision distillation to give 20 parts of perfluoro-Z-heptyne boiling at 5456C.

The products and process of this invention have been illustrated by the foregoing specific examples. However, the invention is generic to all the products defined by the formulas I, II, and III on page 1. Additional examples of the products, together with the acetylenic reactants from which they can be prepared, are shown in the following table:

' TABLE Acetylenic Reactant Products ,192 NF NF,

@Oc c-coou NF II As shown in the following examples, the products of this invention are useful as polymerization initiators.

EXAMPLE A A mixture of parts of tetrafluoroethylene, parts of perfluorodimethylcyclobutane solvent, and 0.03 part of was heated at 145-150C. and autogenous pressure for five hours in a shaker tube similar to that of Example 1. A total of 8.3 parts (83%) of polytetrafluoroethylene was obtained as a white powder.

EXAMPLE B A mixture of 13.8 parts of tetrafluoroethylene, 30 parts of perfiuorodimethylcyclobutane, and 0.025 part of was heated at 107 for 4.5 hours, autogenous pressure, in a shaker tube like that of Example 1. A total of 9.0 parts (65%) of polytetrafluoroethylene was obtained as a white powder.

EXAMPLE C A mixture of 0.21 part of ethylene and 0.013 part of 'trans-CF C(NF )=C(NF )CF initiator was sealed in a collapsible platinum tube, and the tube was heated at 125 for four hours under 1000 atmospheres external pressure. A total of 0.08 part (38%) of polyethylene was obtained as a white powder. In a control experiment in the absence of the initiator, no polymer was obtained.

' EXAMPLE D A mixture of 10 parts of tetrafluoroethylene, 30 parts of perfluorodimethylcyclobutane, and 0.025 part of F CF CF CF was heated at 111C. for 3.17 hours at autogenous pressure in a shaker tube similar to that of Example 1. A total of 8.9 parts (89%) of polytetrafluoroethylene was obtained as a white powder.

Since obvious modifications and equivalents in the invention will be evident to those skilled in the chemical arts, I propose to be bound solely by the appended claims.

The embodiment of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A compound of the group consisting of M fin R-(|I-C-R' land R-C(NF2)=C(NF2)R wherein R and R are selected from the group consisting of hydrocarbon, halohydrocarbon, nitrohydrocarhon, carboxyhydrocarbon, halocarbonylhydrocarbyl,

1 5 4. A compound of the formula NCC(NF )=C( NF- )CN.

5. The compound of the formula 6. The compound of the formula NIF TF2 C6H5-C-CF-C6H5.

7. A compound of the formula C H C(NF )=C(NF )-C H 8. The compound of the formula 2 c H -c--c1r-c0F.

, 9. The compound of the formula 2 f c n -cF- -c-coF.

10. A compound of the formula C H C(NF )=C(NF )-CH 11. The compound of the formula Fa H -CCF-OH 12. The compound of the formula NF NF l 2 ll 0 H -0F0- 7fl 13. A compound of the formula 14. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting at a temperature of up to the productdecomposition temperature, N F with an acetylenic compound of the formula RC E CR' wherein R and R are selected from the group consisting of hydrocarbon, halohydrocarbon, nitrohydrocarbon, carboxyhydrocarbon, halocarbonylhydrocarbyl, cyanohydrocarbyl, hydrocarbyloxycarbonylhydrocarbyl, carbamoylhydrocarbyl, hydrocarbylcarbamoylhydrocarbyl, dihydrocarbylcarbamoylhydrocarbyl, carboxyl, halocarbonyl, cyano, hydrocarbyloxycarbonyl, carbamoyl, hydrocarbylcarbamoyl and dihydrocarbylcarbamoyl, R and R each containing l-l2 carbons and being free of ethylenic unsaturation and of halogen of atomic number greater than 17.

15. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, N 1 with hexafluoro-Z- butyne.

16. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, N F with dicyanoacetylene.

17. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, N F with methylphenylacetylene.

18,.The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, N F with dimethyldiacetylene.

19. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, N F with diphenyldiacetylene.

20. The process of preparing an organic cofnpound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the productdecomposition temperature, NJ, with perfluoro-2- heptyne.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION PATENT N0. 3,886,197 DATED 1 y 7, 975

INVENTOR(S) 1 George N. Sauseri It is certified that error appears in the above-identitied patent and that said Letters Patent are hereby corrected as shown below:

Col. 2, lines 20, 25 and 50 "R' in each instance should be --R"--.

Col. 2, line 52 Replace the 'comma after "III" with a period.

Col. 6, line 5 L Change "weak-strong-weak" to --weakstrong-strong-weak--.

Col. 10, line 17 Change C" to --CEC--.

Signed and Scaled this fourth Day Of May 1976 [SEAL] A ttest:

RUTH C. M ASON C. MARSHALL DANN Arresting Ojjr'cer ('ommissimu'r nj'larr-ms and Trademarks 

1. A COMPOUND OF THE GROUP CONSISTING OF
 2. A compound of the formula CF3-C(NF2) C(NF2)-CF3.
 3. The compound of the formula
 4. A compound of the formula NC-C(NF2) C(NF2)-CN.
 5. The compound of the formula
 6. The compound of the formula
 7. A compound of the formula C6H5-C(NF2) C(NF2)-C6H5.
 8. The compound of the formula
 9. The compound of the formula
 10. A compound of the formula C6H5-C(NF2) C(NF2)-CH3.
 11. The compound of the formula
 12. The compound of the formula
 13. A compound of the formula CF3-C(NF2) C(NF2)-C4F9.
 14. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting at a temperature of up to the product-decomposition temperature, N2F4 with an acetylenic compound of the formula R-C*C-R'' wherein R and R'' are selected from the group consisting of hydrocarbon, halohydrocarbon, nitrohydrocarbon, carboxyhydrocarbon, halocarbonylhydrocarbyl, cyanohydrocarbyl, hydrocarbyloxycarbonylhydrocarbyl, carbamoylhydrocarbyl, hydrocarbylcarbamoylhydrocarbyl, dihydrocarbylcarbamoylhydrocarbyl, carboxyl, halocarbonyl, cyano, hydrocarbyloxycarbonyl, carbamoyl, hydrocarbylcarbamoyl and dihydrocarbylcarbamoyl, R and R'' each containing 1-12 carbons and being free of ethylenic unsaturation and of halogen of atomic number greater than
 17. 15. The process of preparing an organic compound containing nitrogen and fluorine Which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with hexafluoro-2-butyne.
 16. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with dicyanoacetylene.
 17. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with methylphenylacetylene.
 18. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with dimethyldiacetylene.
 19. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with diphenyldiacetylene.
 20. The process of preparing an organic compound containing nitrogen and fluorine which consists of reacting, at a temperature of up to the product-decomposition temperature, N2F4 with perfluoro-2-heptyne. 